<font face="Verdana, Arial, Helvetica, sans-serif" size="2">Originally posted by RustyC:
The O.P didn't say what levels he'd have to spend miles at to get the $500 in exchange, but I assume he has the freedom to do it selectively and applies it only at standard domestic awards, or 25K miles. That would be effectively selling miles at 2 cents each (if you had to go to "Rule Buster" at 50K it'd be selling at 1 cents each).
Even though my own mileage valuation when deciding on mileage runs is 1.5 cents, I'd be hesitant to sell the miles for 2 cents cash unless I had an awful lot of them and didn't have good prospects for burning them off in the next 5 years (i.e. early in career, limited vacation time for years to come, etc.) If you have a lot more miles than time, it makes sense to offload some for cash rather than let them get devalued (all the sale/barter rules notwithstanding).
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All have been standard awards. When NW/UA/DL are tight, I resort to AA which has very good availability if you're a little flexible.
Regarding my pricing, $.02/mile might be a bit on the low side, but:
1) I like my company
2) I take personal satisfaction in booking otherwise expensive itineraries with miles
3) I've found a method that allows me to convert miles into CASH without breaking any rules/laws
4) As previously noted, I don't buy into the idea that premium travel provides a significantly greater bang for the buck